Key West Vacation Rentals

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Key West vacation homes

A building with a red door, a covered porch, and a bamboo plant in the foreground.

1. Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.6 out of 10, Exceptional, (28 reviews)
"Charming, clean accommodations in a conveniently located area of Key West for walking to sites and renting bicycles"
United States
BARBARA Y.
The price is CA $210
CA $596 total
includes taxes & fees
Nov 15 - Nov 16
Road's End | Prime Old Town Location! Updated Home w/ Pool
A patio area with a fountain, seating, and umbrellas.

2. Andros Suite | Perfect Location with Pool!

Andros Suite | Perfect Location with Pool!
Old Town Key West
10.0 out of 10, Exceptional, (6 reviews)
"Great little place 1 block off Duval. A nice quiet oasis from everything a street away. Moon Dog restaurant is around the block and was great for breakfast and dinner. Great kitchen! The mattress upstairs could use a firmer replacement IMHO…overall very good spot!"
United States
Robert J.
The price is CA $210
CA $621 total
includes taxes & fees
Nov 30 - Dec 1
Andros Suite | Perfect Location with Pool!
A porch with wooden chairs and a table, a wooden door with green shutters, and a white railing.

3. Shared Pool & Near Duval - Curry House Room 9

Shared Pool & Near Duval - Curry House Room 9
Old Town Key West
7.4 out of 10, Good, (20 reviews)
"Nice and clean.Quiet and convenient to Duval.We will be back!"
United States
Deborah L.
The price is CA $144
CA $443 total
includes taxes & fees
Nov 18 - Nov 19
Shared Pool & Near Duval - Curry House Room 9
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

4. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (72 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is CA $261
CA $446 total
includes taxes & fees
Dec 1 - Dec 2
Poolside Cottage #411
A wooden deck with a large tree, outdoor seating, and a marina in the background.

5. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is CA $261
CA $446 total
includes taxes & fees
Dec 1 - Dec 2
Poolside Cottage #412
A covered porch with a table and chairs, a view of the street, and a building with a balcony.

6. Casa Havana | Old Town Condo w/ Pool & Balcony

Casa Havana | Old Town Condo w/ Pool & Balcony
Old Town Key West
9.2 out of 10, Wonderful, (12 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
United States
Kim T.
The price is CA $273
CA $1,022 total
includes taxes & fees
Nov 16 - Nov 17
Casa Havana | Old Town Condo w/ Pool & Balcony
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

7. Sea Esta Suite | Located On Iconic Duval w/ Pool

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (58 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is CA $275
CA $1,025 total
includes taxes & fees
Nov 10 - Nov 11
Sea Esta Suite | Located On Iconic Duval w/ Pool
A white building with a porch, surrounded by tropical plants and a pathway leading to the entrance.

8. Shared Pool & Parking - The Cottage at James House

Shared Pool & Parking - The Cottage at James House
Key West Historic District
8.6 out of 10, Excellent, (10 reviews)
"Awesome location! "
United States
Lindsey M.
The price is CA $369
CA $616 total
includes taxes & fees
Nov 9 - Nov 10
Shared Pool & Parking - The Cottage at James House
An aerial view of a beach with clear turquoise waters, a sandy shore, and a dense forested area.

9. Luxury two floor apartment in prime location of famous Duval Street

Luxury two floor apartment in prime location of famous Duval Street
Old Town Key West
9.6 out of 10, Exceptional, (104 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
United States
Gregory L.
The price is CA $417
CA $1,020 total
includes taxes & fees
Nov 16 - Nov 17
Luxury two floor apartment in prime location of famous Duval Street
A clear swimming pool with lounge chairs and palm trees.

10. Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (5 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
United States
Cathy S.
The price is CA $367
CA $788 total
includes taxes & fees
Nov 10 - Nov 11
Slice of Paradise
A patio area with wicker furniture and a grill.

11. Southernmost Retreat | On Duval! With Hot Tub, Patio

Southernmost Retreat | On Duval! With Hot Tub, Patio
Old Town Key West
9.6 out of 10, Exceptional, (35 reviews)
"Awesome place great location communication with host was great would stay here again next time I’m in key west."
United States
Drew L.
The price is CA $468
CA $1,351 total
includes taxes & fees
Dec 6 - Dec 7
Southernmost Retreat | On Duval! With Hot Tub, Patio
A covered outdoor patio with a pool, seating area, and lush greenery.

12. Coconut Palm by Brightwild Island Home w Pool

Coconut Palm by Brightwild Island Home w Pool
2.0 star property
Old Town Key West
The price is CA $706
CA $1,453 total
includes taxes & fees
Nov 17 - Nov 18
Coconut Palm by Brightwild Island Home w Pool
A covered outdoor seating area with a sofa, chairs, and a coffee table.

13. Coconut Palm - Steps from Duval with Private Pool

Coconut Palm - Steps from Duval with Private Pool
Old Town Key West
9.0 out of 10, Wonderful, (39 reviews)
"Great Property Excellent location "
United States
Jim B.
The price is CA $551
CA $1,297 total
includes taxes & fees
Nov 17 - Nov 18
Coconut Palm - Steps from Duval with Private Pool
A bar with a signboard listing various destinations.

14. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (139 reviews)
"We had an awesome stay! We enjoyed being able to use the bikes and have covered parking, too. We would definitely stay here again!"
United States
Melanie K.
The price is CA $312
CA $718 total
includes taxes & fees
Nov 9 - Nov 10
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A swimming pool with a curved edge, surrounded by palm trees and lounge chairs.

15. Poolside Paradise

Poolside Paradise
Stock Island
The price is CA $381
CA $812 total
includes taxes & fees
Nov 9 - Nov 10
Poolside Paradise
A two-story house with a porch, a blue door, and a brick pathway leading to the entrance.

16. Keys Breeze - Walk to Duval, Private Pool

Keys Breeze - Walk to Duval, Private Pool
Old Town Key West
9.8 out of 10, Exceptional, (41 reviews)
"Great place, location, clean and climate controlled. Pool was great and the host was excellent!"
United States
Lisa S.
The price is CA $671
CA $1,558 total
includes taxes & fees
Nov 16 - Nov 17
Keys Breeze - Walk to Duval, Private Pool
A balcony with white railings, palm trees, and a view of a street with parked cars and buildings.

17. Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Old Town Key West
9.4 out of 10, Exceptional, (58 reviews)
"Great location and we would stay here again. "
United States
Brandon A.
The price is CA $509
CA $1,297 total
includes taxes & fees
Nov 9 - Nov 10
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
A wooden deck with two lounge chairs and a gazebo surrounded by lush greenery.

18. Atlantis House Suites

Atlantis House Suites
Midtown
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place to stay ! Located just close enough and just far away enough . Highly recommended "
United States
Aaron J.
The price is CA $557
CA $1,141 total
includes taxes & fees
Nov 9 - Nov 10
Atlantis House Suites
A gated driveway leading to a house with a wooden fence and a concrete path.

19. Conch Cove | Private Oasis with Heated Pool!

Conch Cove | Private Oasis with Heated Pool!
Old Town Key West
9.8 out of 10, Exceptional, (44 reviews)
"Wonderful spot and outstanding property management company. "
United States
Jessica B.
The price is CA $634
CA $1,691 total
includes taxes & fees
Nov 16 - Nov 17
Conch Cove | Private Oasis with Heated Pool!
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

20. Spacious 3-bedroom townhome on Stock Island with resort style pool.

Spacious 3-bedroom townhome on Stock Island with resort style pool.
Stock Island
10.0 out of 10, Exceptional, (8 reviews)
"Perfect for our family trip to Key West. Great location and we enjoyed the pool and nearby restaurants. Easy check in and check out process and clear, timely communication with the owner. "
United States
Samantha P.
The price is CA $422
CA $888 total
includes taxes & fees
Dec 9 - Dec 10
Spacious 3-bedroom townhome on Stock Island with resort style pool.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Learn more about Key West

Stroll Duval Street's colourful shops and bars before catching the sunset celebration at Mallory Square with local performers. Explore Hemingway's historic home where six-toed cats roam freely, then snorkel the vibrant coral reefs just offshore.

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A sign for the Key West Museum of Art & History at the Custom House.

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